Ammonia → 3-Amino-1-phenoxy-3-methylbutan-2-one oxime hydrochloride

HRID 1580590Notes

Reaction equation

HRID 1580590 reaction equation
[Cl:1][C:2]([CH3:15])([CH:4]([N:13]=[O:14])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:3].[NH3:16]>CO>[ClH:1].[NH2:16][C:2]([CH3:15])([CH3:3])[C:4](=[N:13][OH:14])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 21316467(3-Chloro-3-methyl-2-nitrosobutoxy)benzene

Product 1

HCID 867329813-Amino-1-phenoxy-3-methylbutan-2-one oxime hydrochlorideYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-chloro-4-(p-chloro)phenoxy-2-methyl-3-nitrosobutane (V) (34.20 g) in dry methanol (375 ml) was heated to reflux while ammonia gas was passed through until all the solid dissolved (9.5 hours). Filtration and removal of solvents gave a brown solid, which was largely freed of impurities by washing with benzene. Recrystallisation from isopropanol (a small inorganic residue remained) gave the ketoxime hydrochloride (IV) (19.65 g, yield 54%) as colourless crystals, m.p. 225°-227° (decomp.).

Workup

  1. temperaturewas heated
  2. dissolutiondissolved (9.5 hours)
  3. filtrationFiltration and removal of solvents
  4. customgave a brown solid, which
  5. washby washing with benzene
  6. customRecrystallisation from isopropanol (a small inorganic residue

Sources & evidence

ORD record
ord-9bd9c08ff448446fbca5537bebcc2c1a
Source dataset
uspto-grants-1976_01
Patent number
US03933820

Reaction notes

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